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469785

Sigma-Aldrich

Benzyl glycidyl ether

99%

Synonym(s):

(Benzyloxymethyl)oxirane, (±)-O-Benzylglycidol, 1-(Benzyloxy)-2,3-epoxypropane, 2-[(Phenylmethoxy)methyl]oxirane, 2-[[(Benzyloxy)methyl]oxy]oxirane, 3-(Benzyloxy)-1,2-epoxypropane, Glycidyl benzyl ether, [(Phenylmethoxy)methyl]oxirane

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About This Item

Empirical Formula (Hill Notation):
C10H12O2
CAS Number:
2930-05-4
Molecular Weight:
164.20
EC Number:
220-899-5
MDL number:
MFCD00068664
UNSPSC Code:
12352100
PubChem Substance ID:
24870484
NACRES:
NA.22

Assay

99%

refractive index

n20/D 1.5170 (lit.)

bp

70-73 °C/11 mmHg (lit.)

density

1.077 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

C(OCc1ccccc1)C2CO2

InChI

1S/C10H12O2/c1-2-4-9(5-3-1)6-11-7-10-8-12-10/h1-5,10H,6-8H2

InChI key

QNYBOILAKBSWFG-UHFFFAOYSA-N

General description

Benzyl glycidyl ether is a glycidyl derivative. Rac-/(R)-benzyl glycidyl ether participates in the synthesis of atactic and isotactic linear poly(benzyl 1,2-glycerol carbonate)s. Biocatalytic resolution of racemic benzyl glycidyl ether by Talaromyces flavus has been described. Resolution of benzyl glycidyl ether to (S)-benzyl glycidyl ether with 30% ee and (R)-3-benzyloxypropane-1,2-diol with 40% ee by whole Bacillus alcalophilus cells has been reported. It reacts with K-, K+(15-crown-5)2 to afford potassium glycidoxide and bibenzyl.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Precautionary Statements

P302 + P352 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Chun Wei et al.
Biotechnology letters, 34(8), 1499-1503 (2012-04-25)
Talaromyces flavus containing a constitutive epoxide hydrolase (EH) resolved racemic benzyl glycidyl ether and nine derivatives into their (R)-enantiomers. After optimization of the fermentation conditions, the specific EH activity and biomass concentration were improved from 13.5 U/g DCW and 14.8
Selective cleavage of the linear ether bond in benzyl glycidyl ether and triphenylmethyl glycidyl ether by potassium alkalide as two-electron-transfer reagent.
Grobelny Z, et al.
Journal of Organometallic Chemistry, 660(1), 6-13 (2002)
Youlin Pan et al.
Chemistry, an Asian journal, 12(11), 1198-1203 (2017-03-21)
Cyclic azasilanes have been synthesized for the purpose of developing coupling agents appropriate for a variety of nanotechnologies including surface modification of nanoparticles, nanocrystals, mesoporous materials and substrates. N-Methyl-aza-2,2,4-trimethylsilacyclopentane is representative of this class of compounds. Preliminary data for the
Qingjie Zhang et al.
Nanomaterials (Basel, Switzerland), 8(9) (2018-09-12)
A surface-sizing technique was offered to take full advantage of multi-walled carbon nanotubes (MWCNTs) and epoxy resins. Two surface-sizing treated MWCNTs were obtained through a ball-milling treatment of amino-functionalized MWCNTs (MWCNT-NH₂) with n-butyl glycidylether (BuGE) and benzyl glycidylether (BeGE). These
Heng Zhang et al.
Journal of the American Chemical Society, 135(18), 6806-6809 (2013-04-25)
The synthesis and characterization of atactic and isotactic linear poly(benzyl 1,2-glycerol carbonate)s are reported. The poly(benzyl 1,2-glycerol carbonate)s were obtained via the ring-opening copolymerization of rac-/(R)-benzyl glycidyl ether with CO2 using [SalcyCo(III)X] complexes with high carbonate linkage selectivity and polymer/cyclic
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